Acetic Acid → HCID 14071983, compound

HRID 2352560Notes

Reaction equation

HRID 2352560 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](C)[C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1OC)=[C:15]([OH:21])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[C:23]([O-:26])([O-])=O.[K+].[K+].Cl[C:30]1[CH:35]=[N:34][CH:33]=[CH:32][N:31]=1.[C:36](O)(=O)C>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:36][O:26][CH3:23])=[C:15]([O:21][C:30]1[CH:35]=[N:34][CH:33]=[CH:32][N:31]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 73277ChloropyrazineHCID 178470232HCID 178470232, compound

Product 1

HCID 14071983HCID 14071983, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 300 mg of 5-hydroxy-4-methoxy-methyl-β-carboline-3-carboxylic acid ethyl ester in 3 ml of dry dimethyl sulfoxide is combined with 155 mg of K2CO3 and stirred under nitrogen at room temperature for 30 minutes. After adding 0.2 ml of 2-chloropyrazine, the mixture is agitated for 6 hours at 95° C., then poured into 1N acetic acid and extracted with ethyl acetate. Purification over silica gel yields 242 mg (64%), mp 130°-131° C. (diethyl ether).

Workup

  1. stirringthe mixture is agitated for 6 hours at 95° C.
  2. extractionextracted with ethyl acetate
  3. customPurification over silica gel
  4. customyields 242 mg (64%), mp 130°-131° C. (diethyl ether)

Sources & evidence

ORD record
ord-0b139b75cade4efb81991d213b50a151
Source dataset
uspto-grants-1989_10
Patent number
US04877792

Reaction notes

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